First Time Got Dominated by Trans

After all the times I've spent with other transwomen, the urge to feel dominated has been slowly growing on me. Don't get me wrong, I've enjoyed all the times that I've been topped by a transwoman especially with how hot it feels to bottom for them but I've also been wanting to experience what rough sex feels like. All my experiences so far have always been with very nice and considerate transwomen but they weren't really tops to begin with which I understood.

This led me to play with myself for a couple of weeks which was fun at times but I was still yearning for a certain feeling, that in and out movement inside my ass but with someone else controlling the pace. This led me to look for some tops on sites that I frequented and while there were more bottom/versatile transwomen on that site, a few did catch my attention especially with the way they described themselves.

The one that caught my eye was a tall and voluptuous transwoman who described herself on her profile as being a dominant top that liked breaking in boys who think they can handle her dick. I scrolled through the different ads on there but she was seemingly the most approachable of the bunch that I had looked at so i decided to contact her. Our conversation was pretty straightforward, not much small talk in between and it felt like was really nice about being a top and that she would take it easy on me if I had a hard time. Literally on the same day I contacted her, we agreed to meet later on in the night.

This had me distracted for the rest of the day at work, occasionally shifting from my work tab to a tab I had opened on Reddit with Trans Captions and Sissy Hypnos. I must admit that I did feel a bit nervous since this was the first time I was actually going to meet a dominant transwoman so I looked at these different gifs and videos of transwomen fucking a man in the ass, bonus when I found videos of transwomen fucking crossdressers as well.

Once I was home, I immediately went to work on cleaning my body from head to toe. I was distracted the entire time I was showering as I kept imagining what this night would be like and I couldn't help but touch my ass frequently, slipping a finger inside me just thinking about being dominated later tonight. Once I was done cleaning myself up, I went to my wardrobe and put on some black lacey panties before putting on my boy clothes over since I would have to go out later to pick her up from the door. I still had a few hours to burn so I played some sissy sleep hypno and eventually fell asleep.

I woke up a few hours later and when I checked the clock, there was about an hour left before she would come over and meet up with me. I quickly got out of bed and did some last minute cleaning with both myself and my room and after I was finished, she had already told me that she was on her way to me already. I waited nervously in my room, pacing as I was thinking if I was actually ready for this but I told myself that there's no turning back now since she was already on the way.

When she got to my place and I greeted her at the door, to say she was a bombshell would be an understatement. She had long black hair that slightly hid her face as the wind blew, her boobs were about C/D cup size which looked heavy especially when you take into consideration how small her waist was before exploding into a very thick bottom. She wasn't like a Jessica Rabbit type that had unreal curves to her body but the way she was built made it seem like she was pretty close to that. She introduced herself as Cassie and she was very nice and bright for someone who was about to fuck my ass into a pussy later on.

After exchanging small talk between us, we went inside my house and headed for my room. While I was hurriedly cleaning a while ago, I had also smoked a load of weed from my pipe and I thought I had cleared the room of any smell from it but that notion was quickly shot down when she asked me if I smoked weed because she could smell it even a couple of feet away from my room. Since I was already caught, I admitted that I did just smoke to which she excitedly replied that she also wants to smoke to help ease ourselves into the mood.

Once we were done passing the weed between each other, we found ourselves more relaxed and this was when she asked for a kiss. I thought it was simple enough so I just went in for the kiss but I was surprised when she suddenly put her hand behind my head and pushed my lips more into hers, a sign of things to come later on. She then led me to lie down beside her where she took of her cargo pants to reveal her purple panty that was struggling to keep whatever was inside at bay. We talked for a while like this, her asking me why I wanted to be dominated and that it makes sense for her seeing me. She told me how skinny I was and that it actually looked sexy and feminine, telling me how I would probably look cute if I dressed up.

I then told her that I was actually wearing panties right now which she immediately went for to check. She put her hand inside my shorts and felt the lace material of my panties. At first I was worried that she would judge me since I had also experienced before when I was topped by a transwoman that she didn't like me dressing up because she wanted to fuck a man and not a crossdresser. My worries were dashed when she approved of me wearing panties and going as far as saying that she thought it was cute and sexy. Her hands were still prying around in my shorts as I just lay there allowing her to play with my body as she saw fit. After a while, her hand found my hole and started playing with it at first behind the fabric of my lace panties but she then pulled the panties to the side and licked her finger before placing her finger inside me.

She started off still laying down beside me but after a while, she raised herself up and was now sitting on her legs while fingering me. I then reached over to her dick and got it out of her panties which looked tiny while still soft so I tried to jerk her off but I was getting a hold of it properly so I also raised myself up until I was on all fours before leaning down towards her dick taking it inside my mouth.

While she sighed under her breath she told, "That's right. Get that dick hard in your mouth. Feel how big it can get!"

At first all I had in my mouth was a limp dick that felt like I had taken her balls into my mouth but then it slowly started growing and even throbbing inside my mouth, I hadn't even noticed it but my lips were now wrapped around a 7 inch dick standing in attention as I slurped on her cock. She wasn't going to let me do all the work though, while I was still on all fours and leaning into her crotch she started fingering me again. She would match the intensity of fingering me with the intensity of how much I sucked her off which got us into a sort of loop where I would go down on her and she stick her finger all the way in and as I bobbed up, she would pull her finger out. I even tried going down on her completely by taking her in my throat but I needed more practice with my oral skills since I still couldn't get it completely inside my throat. That didn't stop me from salivating all over her dick as she tried fucking my mouth which made me practically drool all over her throbbing cock.

After a few strokes of fucking my face, she suddenly let up and got me off her cock which made me gasp for air since I was barely breathing the entire time she fucked my face. While I adjusted with my breathing and wiping away some of the tears that flowed down my cheek, she just continued to stroke her very wet cock in front of me and she didn't even need to say anything because when she nodded at me I immediately assumed the position to lie down on my back with my legs raised up.

When I was in position, she held one of my thighs with her hand while she stroked with the other. Then taking aim at my hole, she spat at it and then drooled over her cock before stroking it again. She would look at me before looking down at my hole which was a pattern she repeated, almost as if she was gauging whether or not I was ready for her. I don't know how I must've looked like but I just tried to look the sluttiest I could by biting my lips and keeping my eyes low in a seductive manner with my eyebrows scrunched in the middle. How I looked must've sent her over the edge because the hand that was gripping my thigh suddenly tightened up before she lined herself up to my hole and began pushing.

A dildo may seem real and it can get the job the done if done properly but there's just something else about a real penis going inside of you. It was just right in between being hard enough to penetrate me but soft enough that it still conformed to my insides. All the other times I've done it with transwomen have always been slow and steady where I could feel them enter me inch by inch while my insides adjusted to the new visitor, but this time around it was anything but. Once her head slipped in, she didn't waste anytime and started pushing her cock into me altogether which was surprising at first but once I got adjusted to the sudden girth inside me, my hole started feeling more pleasure than pain.

Once she bottomed out on me, she asked me if I was ready to take her to which i measly replied with a nod that every sissy would know about: that quick and enthusiastic nod that you give to your dom when they ask you something, especially if they ask you if you're ready to be thoroughly fucked. She chuckled at the way I nodded when she pulled out a little bit slower than when she went inside me the first time and then pushing back in with one fell swoop into my ass. At first she would take out about 3/4 of her dick out of me and then immediately pushing back all the way in but I didn't feel her crotch smack against my ass but as she picked up her pace, the more she bumped into me and started pushing me into the headboard. While she fucked me like this, I was clenching my left hand over my chest and my right hand was hanging onto the headboard behind me; my body swaying back and forth with her strong thrusts in and out of me.

I hadn't even noticed it but as she went on with fucking me with purpose, my legs were slowly being raised until my knee was now past my chest as she pushed on my thighs even more, her hands buried on them while my feet were dangling pathetically over her shoulders. She would stop from time to time and laugh when she would tell me that she needed to stop otherwise she would've unloaded inside me. My initial request for this night was that I wanted to get a facial from her so when she told me that she wanted to cum inside me so bad, I told her that she didn't need to hold back the next time she felt like she was about to burst inside me.

She fucked me even more which made me moan along with her thrusts. I don't know what came over me but I wrapped my legs around her and held onto her neck before being overcome and telling her, "Yeah? You want to cum inside me? Fill my sissy pussy up!"

I don't really know what came over me at that moment; whether it was the sissy bliss I was feeling whenever she would thrust back into me or just the idea of being used and abused like I was right now but I knew I was really getting into this now and I just wanted to shout out how much I wanted to be a sissy bitch. After I told here this, she just replied with a grunt before seemingly changing gears with her pace and she was now bottoming out on me but with a loud slap every time her crotch met my ass. I could only imagine how I looked like: my legs and knees reaching a flexible place that I never knew I could reach before, my eyes rolling to the back of my head, my mouth open agape as girly moans came from it. This is what sissy dreams are made of.

We must've lasted that way for at least 20 minutes when her pace suddenly slowed down but the power of the thrusts remained the same, if not more powerful. She didn't even tell me but I definitely felt it, she just came inside me and she came a LOT! If you've read my story about my first creampie from a transwoman, I already know what it feels like to have cum deposited inside me but the way Cass filled me up was different from what I experienced the first time.

The first thing I noticed was different was how wet my ass was when she was still thrusting in and out of me even after she already came inside me. In my experience before, my ass was filled up but none of it made it's way out while they fucked me. But with Cassie, she filled me up to the brim and then some. With each thrust inside me more of the cum that was already inside me started leaking out but she didn't really care and kept at it. The second thing I noticed was how hot and sticky her cum was compared to what I experienced before. I literally felt it erupt from her penis and into my anal cavity as each throb of her dick coated my insides with her sweet cum. The heat made me moan in surprise because even the "hot" lubricants that I've used before couldn't compare to the heat that I was feeling from her semen flowing inside me from each spurt of her cock. I just lay there as her grip on my thighs slowly ease up and I could feel her softening penis slowly slip its way out of me.

We stayed like that for a while. I lay there with my chest rising and falling with each breath I took after being manhandled (transhandled?) by Cassie and she just looked at me with a smile that I didn't know how to interpret until she spoke up and said some things about me. She told me how my body was that of a typical twink and it was the first time I've ever heard someone say that I was sexy in a feminine way. She would stroke my hair and my eyebrows as she said she imagined how I would like if I grew my hair and shaped my eyebrows. She even asked me what cup size I would want if I was given the chance to have my own boobs to which I replied an A or B cup would suit me since I was a bit on the lanky side. I felt like she was slowly opening up the idea of feminizing/turning me into a sissy so I just joked about her seemingly wanting to do just that to me and I was expecting her to go along with the joke but she just agreed to what I said. She nodded in agreement that she did actually want to turn me into her own personal sissy.

For someone who has been watching sissy hypnos and reading sissy captions on a daily basis, it felt surreal to me to hear those things said to me. Like all the things I've watched and read were suddenly coming to life and instead of a random girl's voiceover on top of a PMV, it was a real transwoman telling me things that I've always wanted to hear said about me. It felt like one of those moments that sissies always talk about with the "point of no return" and this was definitely my point of no return, that if I accepted her offer my life would change forever. She must've noticed that I was getting deep into my thoughts so she reassured me that those were just things she thought of and not really something she would force on me if I didn't want it. I guess looking back at my experience with Cassie, I really appreciated that she made me feel like a sissy but only up to the point I was comfortable with which made my experience all the more memorable since I was still given the choice on how far we'd go down this rabbit hole of mine.

We then rested for a while where she asked me to cuddle into her which was another first for me since I would normally be the one being cuddled into so I lied down on her breasts which were admittedly a bit stiff but I couldn't deny how hot they looked being so round and firm. She had her arm wrapped around me and was at first just stroking my back up to my shoulders but after a while she told me to place my leg on hers. She then reached down with her arm wrapped around me and gave my ass a few smacks. It still sounded like a slap and you could see a bit of jiggle happening but I also won't deny that I was skinny as fuck which meant my ass looked bonier than usual. I told her that this made me insecure since I thought that being a sissy meant having a nice round and bubble butt. She then reassured me that it wasn't all the case and she liked my ass, she then gave me a few more playful smacks to prove her point.

I don't really remember how long we stayed like that and I don't know how we really changed positions but after a while of cuddling together and a few playful smacks from her, I found myself on all fours again and sucking her cock. It was easier this time around to get her hard since I've already adjusted a while ago but I still gagged from time to time especially when she would hold my head in place and start to thrust herself into my mouth pussy. While I gave her a blowjob, she would scoop up some of her cum leaking out of me and started pushing it back in, fingering me the same way she did the first time around earlier. It didn't take long for me to get her dick absolutely wet again and this time I didn't mind the drool and tears flowing down my face, in my imagination I just looked like an abused sissy whore who wanted nothing but to be a sex doll right now.

At first I was going to lay down on my back again but she had other plans in mind. She grabbed my waist while I was trying to lie down and told me, "Uh-uh. I want to see that ass bounce on my dick this time."

I remembered how insecure I felt about my ass earlier so I told her that it might not be the best view from her perspective but she just reassured me that she'll be the judge of that and to just let her do her thing with me. So I turned and had my ass facing her and I was a bit conscious about the way my bony ass must've looked which was quickly taken away when she suddenly smacked my ass harder than normal, heck even I haven't slapped myself that hard before. She gave me a few more smacks like that and I felt the cool air pass above my probably reddened cheeks which made me slide further down on my chest and it made my ass stick out even more.

Later on, the smacks from her hands were replaced by smacks from her penis as she played with my ass before actually inserting herself into me. She took her sweet time teasing my hole while she would hold her cock and slowly push into my pussy and just as it was going inside, she teases me by pulling away or smacking her cock on my hole a few times. She then told me to relax so I did, making me slide further down on the bed as I felt her slowly entering me. She didn't take her time like last time and probably because of the cum inside me acting as a lubricant, but she just shoved herself into me which ended with a loud slapping noise as our bodies met.

She just let me lay down on my chest while she supported my lower body by holding onto my waist while she pounded my ass into a pussy. The position we were in made it so that she was going straight for my tummy and in a way, she passed by my p-spot repeatedly in this position. This made me moan and squirm like a little sissy bitch that I was. The moans I was practically screaming into the bed sounded so girly to me, my hands not knowing what to do with themselves started reaching out wherever it could to try and grasp at the sheets of the bed or the walls of the room. Like many firsts tonight, this was the first time I found myself in a position like this. Yes I've done it dog style with other transwomen before but they way I was just being used in this position with seemingly no way out even if I wanted to, it just made the experience all the more hot and sexy than it already is.

At one point while she fucked me, we had a mini conversation between us that basically went like this:

Her: "Fuck! It feels like I'm fucking a pussy with how good your ass feels around me."

Me: "Yeah fuck that sissy pussy up! I want to feel every single inch of you inside me, pleaseee!"

Her: "Oh God if you keep that up I might just make you my sissy bitch."

At this point I just looked back at her from my peripherals which made her a bit more feral than she already was because she suddenly picked me up from the bed and started jack-hammering herself into me while holding me up. She then played with my nipples as she mercilessly fucked me ass. Again another first for me when I found myself in this position where she was literally holding me in place to make sure that her penis had the best entry possible into my pussy. I could feel the pressure building up inside me as she constantly hit my p-spot while at the same time she played with my sensitive nipples. If she didn't stop all of a sudden because of how tired she got with how intense we were going, I might have sissygasmed right then and there. That's without saying that I was shaking vigorously after she thoroughly fucked my pussy up, like I was having a dry sissygasm where I felt the euphoria but nothing was coming out.

My legs immediately gave out and at the same time she let go of me at this moment so I just flopped down onto the bed and as I looked to my left, I noticed my reflection in the mirror on the wall: my eyes looked drowsy like I was sleepy but I still wanted to keep going. My back raised ever so slightly and then back down from my breaths, my ass with wet streaks all over the cheeks and just imagining my throbbing clit underneath me just wanting to burst. I thought it was already over since we both must've been tired already but she still had a little bit left in her tank so she just stroked herself to the image of a spent sissy that's been properly fucked by her.

Without warning she mounted me from behind and being the skinny guy I was, I could feel how heavy she was and she literally had me pinned to the bed. If I wanted out, there wasn't going to be any out for me which helped me reinforce the thought that I was indeed a sissy girl that was only meant to satisfy the cravings of her dom. She adjusted for a bit behind me trying to get her hard cock in my soft sissy hole and when she finally got to line up her dick with my pussy, she just pushed in like it was nothing and I could even feel some of the cum from earlier start to leak out. I looked back at the mirror from earlier and saw her raw form of fucking me. Her hair was disheveled and swaying along with her thrusts, her arms were flexed while they supported her upper body, and her lower body from her waist down seemed to have a mind of their own as the rest of her body was steady and only her waist was moving with a seductive sway of her hips.

She mounted me like this for a while, occasionally changing her position by raising one her legs up. At one point, she raised only my ass up with her hands so that I was still lying down on my chest but with my ass ever so slightly raised and she had one of her feet pressed up against my head while she thoroughly fucked me. If I wasn't looking at the mirror and watching how she made me her sissy bitch, I was staring at the wall in front of me as my hands reached everywhere it could just to get a hold of something and to clench my hands with how much pleasure I was feeling. I could feel my eyes roll back further and further into my skull as she thrust inside me and at that point I knew she was just using my pussy to satiate her hunger and it made it all the more hot than it already was.

I had already forgotten about my request to her before we even started any of this and that was that I wanted a facial from her. While she fucked me like this, it was still in the back of my mind that I wanted her to give me a facial but there was also a nagging feeling that I wanted to feel what I felt earlier when she creampied me with all of her cum filling me up. So instead of trying to remind her about the facial, I just raised my ass up even more to the point that I was matching her motions and pushing myself even further and harder into her throbbing cock. She would also occasionally slow down and keep quiet for a few seconds before resuming what she was doing so I also figured that she was getting close and was just edging herself to make the most out of our fucking each other. Her strokes turned from long and deep hitting ones to where she just bottomed out and stuck out an inch or two before going back inside, all in one rapid motion. I also felt a different wetness behind me that wasn't the same as the feeling of sweat or lube so I understood that she had just unloaded in me without telling me and I could feel the semen flow out of me.

With panted breath I asked her, "Did you cum inside me again?"

And while looking at the mirror, I saw her just nod her head in agreement as she was still a bit winded from the fucking she just gave my sissy pussy. This made me chuckle a bit and with the remaining ounce of horny that I still had in me, I pushed back even more when she tried to take her penis out of me. I felt the push of her head on my prostate as it also pushed back in and out the copious amounts of semen I had inside me. When I pushed back at her, she took this as a sign to push even deeper into me as well until she placed her entire weight on me while hugging me. It wasn't enough to suffocate me but it was something I could compare to a tight fitting heavy blanket that licks and kisses your ears and has their softening cock slowly slip out of you while their breasts push on your back while they breath.

When her cock had softened up and slipped out of me, I remember feeling the cool air suddenly wash over my pussy with some of the cum leaking out and even forming bubbles that were audible when they popped. I lay there just thinking about what had just happened and the fact that I allowed all of it to happen, that I wanted to be fucked like the sissy bitch I was and that was exactly what I got. While I zoned out on the bed, I heard her go into the restroom and started cleaning herself up so I got up and followed her into the restroom to clean up as well. While in the shower, she offered to help me clean up so I just intentionally clenched my ass before she cleaned me up in order to make sure that no semen gets cleaned out.

After we got cleaned up and fixed ourselves, we cuddled again for a while before she asked for another load of weed before she left. While we were smoking, she reminded me about how pretty I would be as a girl and even told me to look at the mirror while she told me about how we could make so much money together by recording videos together. How she would be my domme and I would be her sissy slave, slowly becoming more and more feminine as time passes. During that moment, I felt what must've been sissy bliss that I was finally hearing the things I've always wanted to hear when watching sissy hypnos and that I was getting support for this side of mine.

After she left, the first thing I did was to go up to the mirror in the room and kneeling in front of it. I turned around and pointed my pussy at the mirror and at first I tried to push out but there wasn't any coming out which made me worry but in a horny way in the sense that I was worried the semen was stuck inside me but it made me horny thinking about it as well. I adjusted the way I was lying down and having my ass pointed at the mirror, I pushed out again and this time the semen not only leaked out and went down my crotch to my thighs. This time when I pushed out there was an audible sound almost like a wet fart before I saw the semen shoot out of my ass and unto the mirror, splattering across the mirror. I tried to push out the same way but instead of shooting out of me, the cum just kept leaking out of at this point.

Before I could even think about it, I immediately turned around again and lowered myself where the cum had splattered and without hesitation I licked up the cum that just came from my ass. It tasted surprisingly sweet and I don't really know how to explain why I know the taste but it also tasted like my sweet pussy as well. This was surprising to me because even when I watch JOI's or CEI's, I have a hard time trying to eat my cum right after I orgasm so I guess the fact that it wasn't my own cum and it didn't come of my penis made it easier for me to lap up the semen on the mirror.

Overall this experience has made me rethink my sexuality and how I want to go about my life a lot more than any sissy hypno would have. I'm still leaning towards having a balance with my life that I can't just go full sissy especially when it comes to HRT, but I also can't deny that I love the feeling of being topped and properly fucked, especially by a beautiful transwoman such as Cassie. I look forward to the next time that she dominates me, who knows she might not be the only one dominating me by then.

Author's Note:

Thank you once again for reading one of my stories. I've been busy lately with work and have been struggling lately so haven't been able to spend time with a transwoman until recently again. The story and what happened is all true, I just took some liberty with some of the dialogue to make it feel sexier than what it really was (we fucked a lot and spoke very little). I hope you enjoyed this experience of mine and if you haven't, please feel free to check out my other stories and leave a comment on any of them as I enjoy engaging with my readers.